Staff Product Manager - Checkout at Paddle

What do we do? Paddle offers digital product companies a completely different approach to their payment infrastructure. Instead of assembling and maintaining a complex stack of payments-related apps and services, we’re a Merchant of Record for our customers. That means we take away 100% of the pain of payment fragmentation. It’s faster, safer, cheaper, and, above all, way better.  We’re backed by investors including KKR, FTV Capital, Kindred, Notion, and 83North and serve over 6000 software sellers in 245 territories globally.  The Role:   We are looking for an exceptional Staff Product Manager to lead our flagship Checkout experience – the most strategically critical, highest-visibility product surface at Paddle. Every dollar our customers earn flows through Checkout, and the decisions made here directly move the needle on conversion, revenue, and customer trust. This is the toughest product role at Paddle, and we're looking for someone who is energised by that. You will own the Checkout product end-to-end: its strategy, its roadmap, its performance, and its commercial outcomes. You'll operate as the senior product voice in the room with our executive team, engineering leaders, and largest customers, and you'll be expected to set the bar – not just for what we ship, but for how the wider product org makes decisions, runs discovery, and uses data. You'll work in a trio with a strong engineering lead and an experienced product designer, with daily exposure to Sales, Solutions, Customer Success, Risk, Finance, and Exco. Given the cross-functional intensity of the work, this role requires regular in-person collaboration with the Checkout team and the wider Payments group. This is an opportunity for a staff-level operator who wants to own a product that genuinely matters – one with hard technical problems, real commercial stakes, and the platform to influence company strategy. What you'll do:  Strategy & Roadmap Ownership: - Own the long-term vision and strategy for Checkout, grounded in market trends, payments innovation, customer needs, and Paddle's commercial goals. Translate this into a roadmap you can defend at Exco and to customers. - Make – and stand behind – the tough prioritisation calls. Navigate ambiguous, multi-stakeholder trade-offs where the "right" answer requires deep judgement across technical constraints, commercial impact, compliance, and UX. - Set the bar for discovery and prioritisation across the wider Payments group; coach other PMs on how to do this well. Product Development & Delivery: - Lead end-to-end delivery of complex, multi-faceted initiatives without needing oversight. Define and enforce the delivery standards (discovery, specs, experimentation, launch quality) that the rest of the product team operates against. - Work in a tight trio with engineering and design to ship fast, instrument well, and iterate based on real customer signal. Use AI tooling to compress the loop from idea to spec to prototype – we expect ideas to be testable in days, not weeks. - Run a continuous programme of optimisation – A/B tests, beta programmes, usability research – to compound conversion and UX gains across a high-volume, consumer-facing surface. Data, Metrics & Commercial Impact: - Own the KPIs that matter for Checkout (conversion, authorisation rates, revenue impact, NPS, etc.) and weave them into the strategic narrative for the business. - Dive into data independently. We don't expect you to wait for an analyst; we expect you to pull the numbers (with AI help where it accelerates you), form a hypothesis, and bring a recommendation. - Use product data to influence business strategy beyond your immediate roadmap – pricing, GTM, risk policy, settlement, etc. Stakeholder Management & Storytelling: - Align senior stakeholders – including Exco, Sales leadership, and key customers – around the Checkout strategy. Tailor the message, never the substance. - Craft compelling written narratives. At staff level we expect your docs to be the artefact that drives decisions, not a deck or a meeting. - Be a credible technical partner to engineering on complex payments, integrations, and platform decisions. GTM & Customer Proximity: - Oversee GTM for Checkout launches across multiple customer segments and geographies, working with Marketing, Sales, Solutions, and Support. - Shape the customer-centric culture of the team – consistently in front of customers yourself, and building the processes that keep the rest of the team close to them too. We'd love to hear from you if you: - You're used to owning a high-stakes, high-complexity product end-to-end with clear, measurable business impact – or you're a senior PM who is unambiguously operating beyond your title. - You have specific, hands-on experience with payments, checkout, or comparable consumer-facing fintech experiences at scale. You understand auth rates, 3DS, SCA, PSP economics, fraud trade-offs, etc. - You've worked on high-volume, consumer-facing products where small UX or technical changes have outsized commercial impact, and you can talk through specific wins you've owned. - You're technically credible – comfortable in the details with engineers, able to reason about systems, APIs, and trade-offs without needing them to translate. - You're data-fluent and metrics-led. You don't believe a thing until you've seen the numbers, and you can run your own analysis end-to-end. - You use AI as a daily force multiplier – for research, writing, analysis, and building functional prototypes – and can show specific examples of how it's changed the quality and speed of your output. You'll be working alongside engineers and designers who are pushing the same boundary. - You've built and shipped in scale-up or startup environments, including zero-to-one work. You're at home with ambiguity, not blocked by it. - You're an outstanding written and verbal communicator – English is your primary working language, and your writing changes minds. - You're comfortable managing hard trade-offs across customers, Sales, Engineering, Compliance, and Exco – and you stay constructive when the room is tense. - You value regular, in-person collaboration with your team and wider stakeholders – this role isn't a fit for fully remote working. Everyone is welcome at Paddle At Paddle, we’re committed to removing invisible barriers, both for our customers and within our own teams. We recognise and celebrate that every Paddler is unique and we welcome every individual perspective. As an inclusive employer we don’t care if, or where, you studied, what you look like or where you’re from. We’re more interested in your craft, curiosity, passion for learning and what you’ll add to our culture. We encourage you to apply even if you don’t match every part of the job ad, especially if you’re part of an underrepresented group. Please let us know if there’s anything we can do to better support you through the application process and in the workplace. We will do everything we can to support any accommodations needed. We’re committed to building a diverse team where everyone feels safe to be their authentic self. Let’s grow together. Our Values - Paddle Together - “None of us, is as smart as all of us” - Paddle Simply - “Simple can be harder than complex: you have to get your thinking clean to make it simple” - Paddle for others - “We can realise our wildest dreams, so long as we help enough other people to realise theirs” Why you’ll love working at Paddle We are a diverse, growing group of Paddlers across the globe who pride ourselves on our transparent, collaborative and respectful culture. We are a ‘digital-first’ company, which means you can work remotely, from one of our stylish hubs, or even a bit of both! We offer all team members unlimited holidays and 4 months paid family leave regardless of gender. We invest in learning and will help you with your personal development via constant exposure to new challenges, an annual learning fund, and regular internal and external training.